Acetic Acid → N-[(4-Chlorophenyl)methyl]glycine ethyl ester

HRID 408586Notes

Reaction equation

HRID 408586 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:8])[CH2:6][NH2:7])[CH3:3].[Cl:9][C:10]1[CH:17]=[CH:16][C:13]([CH:14]=O)=[CH:12][CH:11]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH2:2]([O:4][C:5](=[O:8])[CH2:6][NH:7][CH2:14][C:13]1[CH:16]=[CH:17][C:10]([Cl:9])=[CH:11][CH:12]=1)[CH3:3]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 77264-ChlorobenzaldehydeHCID 2723640Glycine ethyl ester, hydrochlorideHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 5212684N-[(4-Chlorophenyl)methyl]glycine ethyl ester

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
20 °C

Procedure

To a suspension of glycine ethyl ester hydrochloride (1.2 eq.) in DCE was added TEA (2 eq.) The reaction was stirred for 10 min at 20° C. then 4-chlorobenzaldehyde (1 eq.), acetic acid (4 eq.) and sodium triacetoxyborohydride (2 eq.) were added. The reaction was stirred for 15 h at 20° C. The crude was partitioned between DCM and a saturated aqueous solution of NaHCO3. The aqueous layer was then extracted twice with DCM. The organic layers were combined, washed with brine, dried on MgSO4, filtered and concentrated under reduced pressure to afford (4-chloro-benzylamino)-acetic acid ethyl ester.

Workup

  1. stirringThe reaction was stirred for 15 h at 20° C
  2. customThe crude was partitioned between DCM
  3. extractionThe aqueous layer was then extracted twice with DCM
  4. washwashed with brine
  5. customdried on MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1b5ca0f71b334663ae6555226dfdc5c2
Source dataset
uspto-grants-2014_06
Patent number
US08759334B2

Reaction notes

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